The present invention relates to azole derivatives, to processes for preparing them, to fungicidal, insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them, to methods of using them to combat fungal diseases (especially fungal diseases of plants) and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
Azole and azine derivatives are disclosed in WO95/31448, WO97/18198, WO98/02424, WO98/05670 and WO98/17630.
The present invention provides a compound of formula (I): 
where A is optionally substituted C1-6 alkylene, optionally substituted C2-6 alkenylene, optionally substituted C2-6 alkynylene, optionally substituted cycloalkylene, optionally substituted C1-6 alkylenoxy, optionally substituted oxy(C1-6)alkylene, optionally substituted C1-6 alkylenethio, optionally substituted thio(C1-6)alkylene, optionally substituted C1-6 alkylenamino, optionally substituted amino(C1-6)alkylene, optionally substituted [C1-6 alkyleneoxy(C1-6)alkylene], optionally substituted [C1-6 alkylenethio(C1-6)alkylene], optionally substituted [C1-6 alkylenesulfinyl(C1-6)alkylene], optionally substituted [C1-6 alkylenesulfonyl(C1-6)alkylene] or optionally substituted [C1-6 alkyleneamino(C1-6)alkylene]; provided that A is not CH2 or CH2O; B is N,N-oxide or CR8; Y is O, S or NR9; Z is O, S or NR10; R1 is hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C3-7 cycloalkyl, cyano, nitro or SF5; R2 is hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C1-6 alkynyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, cyano, nitro, formyl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, SF5 or R11ONxe2x95x90C(R12); or R1 and R2 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated, carbocylic or heterocyclic ring which may contain one or two heteroatoms selected from O, N or S and which is optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen; R3 is hydrogen, optionally substituted C1-10 alkyl, optionally substituted [C2-6 alkenyl(C1-6)alkyl], optionally substituted [C2-6 alkynyl(C1-6)alkyl], optionally substituted C3-7 cycloalkyl, optionally substituted C1-10 alkylcarbonyl, optionally substituted C1-10 alkoxycarbonyl, formyl, optionally substituted C1-10 alkylaminocarbonyl, optionally substituted di(C1-10)alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C1-6 arylthio, optionally substituted C1-6 arylsulfinyl, optionally substituted C1-6 arylsulfonyl or R13R14NS(O)p; p is 0, 1 or 2; R4, R5 and R6 are, independently, hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, cyano, nitro, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl or SF5; R7 is hydrogen, halogen, cyano, optionally substituted C1-20 alkyl, optionally substituted C2-20 alkenyl, optionally substituted C2-20 alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted C5-6 cycloalkenyl, formyl, optionally substituted C1-20 alkoxycarbonyl, optionally substituted C1-20 alkylcarbonyl, aminocarbonyl, optionally substituted C1-20 alkylaminocarbonyl, optionally substituted di(C1-20)alkylaminocarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyl, optionally substituted arylaminocarbonyl optionally substituted Nxe2x80x94(C1-6)alkyl-N-arylaminocarbonyl, optionally substituted diarylaminocarbonyl, optionally substituted heteroaryloxycarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted heteroarylaminocarbonyl, optionally substituted Nxe2x80x94(C1-6)alkyl-N-heteroarylaminocarbonyl, optionally substituted diheteroarylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, SH, optionally substituted C1-20 alkylthio, optionally substituted C1-20 alkylsulfinyl, optionally substituted C1-20 alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl, R15O, R16R17N or R18ONxe2x95x90C(R19); R8 is hydrogen, halogen, nitro, cyano, optionally substituted C1-8 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkylaminocarbonyl, optionally substituted di(C1-6)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryl; R9 is hydrogen, cyano, nitro, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted (C2-4)alkenyl(C1-6)alkyl, optionally substituted (C2-6)alkynyl(C1-6)alkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylamino, optionally substituted di(C1-6)alkylamino, optionally substituted C1-6 alkylcarbonylamino, optionally substituted C1-6 alkoxycarbonylamino, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl or C1-6 alkylcarbonyloxy; R10 is hydrogen, cyano, optionally substituted C1-8 alkyl, optionally substituted [C2-6 alkenyl(C1-6)alkyl], optionally substituted [C2-6 alkyl(C1-6)alkyl], optionally substituted C3-7 cycloalkyl, optionally substituted [C3-7 cycloalkyl(C1-6)alkyl], C1-6 alkoxy(C1-6)alkyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkylaminocarbonyl, optionally substituted di(C1-6)alkylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted alkylsulfonyl or optionally substituted arylsulfonyl; R11 and R18 are, independently, hydrogen, optionally substituted phenyl (C1-2)alkyl or optionally substituted C1-20 alkyl; R12 and R19 are, independently, hydrogen, optionally substituted phenyl or optionally substituted C1-6 alkyl; R13 and R14 are, independently, optionally substituted C1-6 alkyl; or R13 and R14 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N and S and which is optionally substituted by one or two independently selected C1-6 alkyl groups; R15 is hydrogen, optionally substituted C1-20 alkyl, optionally substituted [C2-20 alkenyl(C1-6)alkyl], optionally substituted [C2-20 alkynyl(C1-6)alkyl], optionally substituted C3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, (C1-6)alkylCHxe2x95x90N, optionally substituted arylCHxe2x95x90N, optionally substituted [aryl(C1-6)alkyl]CHxe2x95x90N, optionally substituted heteroarylCHxe2x95x90N, optionally substituted [heterocyclyl(C1-6)alkyl]CHxe2x95x90N, optionally substituted arylC(CH3)xe2x95x90N, optionally substituted heteroarylC(CH3)xe2x95x90N or optionally substituted di(C1-6)alcylCxe2x95x90N; and R16 and R17 are, independently, hydrogen, optionally substituted C1-20 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted [C2-20 alkenyl(C1-6)alkyl], optionally substituted [C2-20 alkynyl(C1-6)alkyl], optionally substituted C1-20 alkoxycarbonyl, optionally substituted phenoxycarbonyl, formyl, optionally substituted C1-20 alkylcarbonyl, optionally substituted C1-20 alkylsulfonyl or optionally substituted phenylsulfonyl.
One group of preferred compounds of formula (I) is a group wherein A is optionally substituted C1-6 alkylene, optionally substituted C2-6 alkenylene, optionally substituted C2-6 alkynylene, optionally substituted C1-6 alkylenoxy, optionally substituted oxy(C1-6)alkylene, optionally substituted C1-6 alkylenethio, optionally substituted thio(C1-6)alkylene, optionally substituted C1-6 alkylenamino, optionally substituted amino-(C1-6)alkylene, optionally substituted [C1-6 alkyleneoxy(C1-6)aklylene], optionally substituted [C1-6 alkylenethio(C1-6)alkylene], optionally substituted [C1-6 alkylenesulfinyl(C1-6)alkylene], optionally substituted [C1-6 alkylenesulfonyl(C1-6)alkylene] or optionally substituted [C1-6 alkyleneamino(C1-6)alkylene], provided that A is not CH2 or CH2O; B is N,N-oxide or CR8; Y is O, S or NR9; Z is O, S or NR10; R3 is hydrogen, optionally substituted C1-10 alkyl, optionally substituted [C2-6 alkenyl(C1-6)alkyl], optionally substituted [C2-6 alkynyl(C1-6)alkyl], optionally substituted C3-7 cycloalkyl, optionally substituted C1-10 alkylcarbonyl, optionally substituted C1-10 alkoxycarbonyl, formyl, optionally substituted C1-10 alkylaminocarbonyl, optionally substituted di(C1-10)alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C1-6 arylthio, optionally substituted C1-6 arylsulfinyl, optionally substituted C1-6 arylsulfonyl or R13R14NS; R4, R5 and R6 are, independently, hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, cyano, nitro, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl or SF5; R7 is hydrogen, halogen, cyano, optionally substituted C1-20 alkyl, optionally substituted C2-20 alkenyl, optionally substituted C2-20 alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted C5-6 cycloalkenyl, formyl, optionally substituted C1-20 alkoxycarbonyl, optionally substituted C1-20 alkylcarbonyl, aminocarbonyl, optionally substituted C1-20 alkylaminocarbonyl, optionally substituted di(C1-20)alkylaminocarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyl, optionally substituted arylaminocarbonyl, optionally substituted N-alkyl-N-arylamimocarbonyl, optionally substituted diarylaminocarbonyl, optionally substituted heteroaryloxycarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted heteroarylaminocarbonyl, optionally substituted alkylheteroarylaminocarbonyl, optionally substituted diheteroarylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, R15O, HS, optionally substituted C1-20 alkylthio, optionally substituted C1-20 alkylsulfinyl, optionally substituted C1-20 alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl, R16R17N or R18ONxe2x95x90C(R19); R1 is hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C3-7 cycloalkyl, cyano, nitro or SF5; R2 is hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, cyano, nitro, formyl, R11ONxe2x95x90C(R12), optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl or SF5; or R1 and R2 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two heteroatoms selected from O, N or S and which may be optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen; R9 is hydrogen, cyano, nitro, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted (C2-6)alkenyl(C1-6)alkyl, optionally substituted (C2-6)alkynyl(C1-6)alkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylamino, optionally substituted di(C1-6)alkylamino, optionally substituted C1-6 alkylcarbonylamino, optionally substituted C1-6 alkoxycarbonylamino, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl or C1-6 acyloxy, R10 is hydrogen, cyano, optionally substituted C1-8 alkyl, optionally substituted [C2-6 alkenyl(C1-6)alkyl], optionally substituted [C2-6 alkynyl(C1-6)alkyl], optionally substituted C3-7 cycloalkyl, optionally substituted [C3-7 cycloalkyl(C1-6)alkyl], C1-6 alkoxy(C1-6)alkyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkylaminocarbonyl, optionally substituted di(C1-6)alkylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted alkylsulfonyl or optionally substituted arylsulfonyl; R8 is hydrogen, halogen, nitro, cyano, optionally substituted C1-8 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 cycloalkyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkylaminocarbonyl, optionally substituted di(C1-6)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryl; R13 and R14 are, independently, optionally substituted CC1-6 alkyl or R13 and R14 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups; R15 is hydrogen, optionally substituted C1-20 alkyl, optionally substituted [C2-20 alkenyl(C1-6)alkyl], optionally substituted [C1-20 alkynyl(C1-6)alkyl], optionally substituted C3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted [heterocyclyl(C1-6)alkylCHxe2x95x90N] or di(C1-6)alkylCxe2x95x90N; R16 and R17 are, independently, hydrogen, optionally substituted C1-20 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted [C2-20 alkenyl(C1-6)alkyl], optionally substituted [C2-20 alkynyl(C1-6)alkyl], optionally substituted C1-20 alkoxycarbonyl, optionally substituted phenoxycarbonyl, formyl, optionally substituted C1-20 alkylcarbonyl, optionally substituted C1-20 alkylsulfonyl or optionally substituted phenylsulfonyl; or R16 and R17 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups; R19 and R12 are independently hydrogen, optionally substituted phenyl or optionally substituted C1-6 alkyl; and R18 and R11 are, independently, hydrogen, optionally substituted phenyl (C1-2)alkyl or optionally substituted C1-20 alkyl.
The compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
When present, optional substituents on alkylene, alkenylene or alkynylene moieties include (subject to valency constraints) one or more of hydroxy, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C1-6 alkoxy(C1-6) alkyl, C1-6 alkoxy, cyano, xe2x95x90O, xe2x95x90NR20 and xe2x95x90CR21R22; and, especially, one or more of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl C1-6 alkoxy(C1-6) alkyl, C1-6 alkoxy, cyano, xe2x95x90O, xe2x95x90NR20 and xe2x95x90CR21R22; wherein R20 is C1-6 alkyl, C1-6 haloalkyl, OR23 or NR24R25; where R21 and R22 are, independently, hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, cyano, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl or NR26R27; R23 is C1-6 alkyl, C1-6 haloalkyl or phenyl(C1-2)alkyl; R24 and R25 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C2-6 alkenyl(C1-6)alkyl, C2-6 alkynyl(C1-6)alkyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, carboxy(C1-6)alkyl or phenyl(C1-2)alkyl; or R24 and R25 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which is optionally substituted by one or two C1-6 alkyl groups; R26 and R27 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C2-6 alkenyl(C1-6)alkyl, C2-6 alkynyl(C1-6)alkyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, carboxy(C1-6)alkyl or phenyl(C1-2)alkyl; or R26 and R27 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which is optionally substituted by one or two C1-6 alkyl groups.
Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or neopentyl.
When present, the optional substituents on an alkyl moiety include one or more of halogen, nitro, cyano, NCSxe2x80x94, C3-7 cycloalkyl (itself optionally substituted with C1-6 alkyl or halogen), C5-7 cycloalkenyl (itself optionally substituted with C1-6 alkyl or halogen), hydroxy, C1-10 alkoxy, C1-10 alkoxy(C1-10)alkoxy, tri(C1-4)alkylsilyl(C1-6)alkoxy, C1-6 alkoxycarbonyl(C1-10)alkoxy, C1-10 haloalkoxy, aryl(C1-4)alkoxy (where the aryl group is optionally substituted), C3-7 cycloalkyloxy (where the cycloalkyl group is optionally substituted with C1-6 alkyl or halogen), C1-10 alkenyloxy, C1-10 alkynyloxy, SH, C1-10 alkylthio, C1-10 haloalkylthio, aryl(C1-4)alkylthio (where the aryl group is optionally substituted), C3-7 cycloalkylthio (where the cycloalkyl group is optionally substituted with C1-6 alkyl or halogen), tri(C1-4)alkylsilyl(C1-6)alkylthio, arylthio (where the aryl group is optionally substituted), C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, arylsulfonyl (where the aryl group may be further optionally substituted), tri(C1-4)alkylsilyl, aryldi(C1-4)alkylsilyl, (C1-4)alkyldiarylsilyl, triarylsilyl, C1-10 alkylcarbonyl, HO2C, C1-10 alkoxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di(C1-6 alkyl)aminocarbonyl, NCxe2x80x94(C1-3 alkyl)-Nxe2x80x94(C1-3 alkoxy)aminocarbonyl, C1-6 alkylcarbonyloxy, arylcarbonyloxy (where the aryl group is optionally substituted), di(C1-6)alkylaminocarbonyloxy, aryl (itself optionally substituted), heteroaryl (itself optionally substituted), heterocyclyl (itself optionally substituted with C1-6 alkyl or halogen), aryloxy (where the aryl group is optionally substituted), heteroaryloxy, (where the heteroaryl group is optionally substituted), heterocyclyloxy (where the heterocyclyl group is optionally substituted with C1-6 alkyl or halogen), amino, C1-6 alkylamino, di(C1-6)alkylamino, C1-6 alkylcarbonylamino and Nxe2x80x94(C1-6)alkylcarbonyl-Nxe2x80x94(C1-6)alkylamino.
Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E) or (Z)-configuration. Examples are vinyl, allyl and propargyl.
When present, the optional substituents on alkenyl or alkynyl include those optional substituents given above for an alkyl moiety.
In the context of this specification acyl is optionally substituted C1-6 alkylcarbonyl (for example acetyl), optionally substituted C2-6 alkenylcarbonyl, optionally substituted C2-6 alkynylcarbonyl, optionally substituted arylcarbonyl (for example benzoyl) or optionally substituted heteroarylcarbonyl.
Halogen is fluorine, chlorine, bromine or iodine.
Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF3, CF2Cl, CF3CH2 or CHF2CH2.
Aryl includes naphthyl, anthracyl, fluorenyl and indenyl but is preferably phenyl.
The term heteroaryl refers to an aromatic ring containing up to 10 atoms including one or more heteroatoms (preferably one or two heteroatoms) selected from O, S and N. Examples of such rings include pyridine, pyrimidine, furan, quinoline, quinazoline, pyrazole, thiophene, thiazole, oxazole and isoxazole.
The terms heterocycle and heterocyclyl refer to a non-aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected from O, S and N. Examples of such rings include 1,3-dioxolane, tetrahydrofuran and morpholine.
When present, the optional substituents on heterocyclyl include C1-6 alkyl as well as those optional substituents given above for an alkyl moiety.
Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.
Cycloalkenyl includes cyclopentenyl and cyclohexenyl.
When present, the optional substituents on cycloalkyl or cycloalkenyl include C1-3 alkyl as well as those optional substituents given above for an alkyl moiety.
Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.
When present, the optional substituents on aryl or heteroaryl are selected, independently, from halogen, nitro, cyano, NCSxe2x80x94, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C3-7 cycloalkyl (itself optionally substituted with C1-6 alkyl or halogen), C5-7 cycloalkenyl (itself optionally substituted with C1-6 alkyl or halogen), hydroxy, C1-10 alkoxy, C1-10 alkoxy(C1-10)alkoxy, tri(C1-4)alkylsilyl(C1-6)alkoxy, C1-6 alkoxycarbonyl(C1-10)alkoxy, C1-10 haloalkoxy, aryl(C1-4)alkoxy (where the aryl group is optionally substituted), C3-7 cycloalkyloxy (where the cycloalkyl group is optionally substituted with C1-6 alkyl or halogen), C1-10 alkenyloxy, C1-10 alkynyloxy, SH, C1-10 alkylthio, C1-10 haloalkylthio, aryl(C1-4)alkylthio (where the aryl group may be further optionally substituted), C3-7 cycloalkylthio (where the cycloalkyl group is optionally substituted with C1-6 alkyl or halogen), tri(C1-4)alkylsilyl(C1-6)alkylthio, arylthio (where the aryl group is optionally substituted), C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, arylsulfonyl (where the aryl group is optionally substituted), tri(C1-4)alkylsilyl, aryldi(C1-4)alkylsilyl, (C1-4)alkyldiarylsilyl, triarylsilyl, C1-10 alkylcarbonyl, HO2C, C1-10 alkoxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di(C1-6 alkyl)aminocarbonyl, Nxe2x80x94(C1-3 alkyl)-Nxe2x80x94(C1-3 alkoxy)aminocarbonyl, C1-6 alkylcarbonyloxy, arylcarbonyloxy (where the aryl group is optionally substituted), di(C1-6)alkylaminocarbonyloxy, aryl (itself optionally substituted), heteroaryl (which itself may be further optionally substituted), heterocyclyl (itself optionally substituted with C1-6 alkyl or halogen), aryloxy (where the aryl group is optionally substituted), heteroaryloxy (where the heteroaryl group is optionally substituted), heterocyclyloxy (where the heterocyclyl group is optionally substituted with C1-6 alkyl or halogen), amino, C1-6 alkylamino, di(C1-6)alkylamino, C1-6 alkylcarbonylamino and Nxe2x80x94(C1-6)alkylcarbonyl-Nxe2x80x94(C1-6)alkylamino.
For substituted phenyl moieties, heterocyclyl and heteroaryl groups it is preferred that one or more substituents are independently selected from halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C3-7 cycloalkyl, nitro, cyano, CO2H, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, R28R29N or R30R31NC(O); wherein R28, R29, R30 and R31 are, independently, hydrogen or C1-6 alkyl.
Haloalkenyl groups are alkenyl groups which are substituted with one or more of the same or different halogen atoms.
It is to be understood that dialkylamino substituents include those where the dialkyl groups together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which is optionally substituted by one or two independently selected (C1-6)alkyl groups. When heterocyclic rings are formed by joining two groups on an N atom, the resulting rings are suitably pyrrolidine, piperidine, thiomorpholine and morpholine each of which may be substituted by one or two independently selected (C1-6) alkyl groups.
Preferably the optional substituents on an alkyl moiety include one or more of halogen, nitro, cyano, HO2C, C1-6 alkoxy (itself optionally substituted by C1-10 alkoxy), aryl(C1-4)alkoxy, C1-10 alkylthio, C1-10 alkylcarbonyl, C1-10 alkoxycarbonyl, C1-6 alkylaminocabonyl, di(C1-6 alkyl)aminocarbonyl, (C1-6)alkylcarbonyloxy, optionally substituted phenyl, heteroaryl, aryloxy, arylcarbonyloxy, heteroaryloxy, heterocyclyl, heterocyclyloxy, C3-7 cycloalkyl (itself optionally substituted with (C1-6)alkyl or halogen), C3-7 cycloalkyloxy, C5-7 cycloakenyl, C1-6 alkylsulfonyl, C1-6 alkylsulfyl, tri(C1-4)alkylsilyl, tri(C1-4)alkylsilyl(C1-6)alkoxy, aryldi(C1-4)alkylsilyl, (C1-4)alkyldiarylsilyl and triarylsilyl.
Preferably the optional substituents on alkenyl or alkynyl include one or more of halogen, aryl and C3-7 cycloalkyl.
It is more preferred that heterocyclyl is optionally substituted by C1-6 alkyl.
Preferably the optional substituents for cycloalkyl include halogen, cyano and C1-3 alkyl.
Preferably the optional substituents for cycloalkenyl include C1-3 alkyl, halogen and cyano.
In a further aspect, the present invention provides a compound of formula (IA): 
wherein A, B, Y, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above for a compound of formula (I).
More preferred compounds of formula (IA) are those wherein R1 is hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 cyanoalkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C3-6 cycloalkyl, C3-7 cycloalkyl(C1-4)alkyl, C1-6 alkoxy(C1-6)alkyl, cyano, nitro or SF5; A is C1-6 alkylene, C1-6 alkenylene, C1-6 alkylenoxy, oxy(C1-6)alkylene, C1-6 alkylenamino or C1-6 alkylenethio, each of which is optionally substituted by C1-3 alkyl, C1-3 haloalkyl, C1-3 cyanoalkyl, halogen, C1-3 alkoxy, C1-6 alkoxycarbonyl, cyano, xe2x95x90O, xe2x95x90NR20 or xe2x95x90CR21R22, provided that A is not CH2 or CH2O; B is N or CR8; Y is O, S or NR9; Z is O, S or NR10; R3 is hydrogen, C1-10 alkyl, benzyloxymethyl, benzoyloxymethyl, C1-6alkoxy(C1-6)alkyl, C2-6 alkenyl(C1-6)alkyl (especially allyl), C2-6 alkynyl(C1-6)alkyl (especially propargyl), C1-10 alkylcarbonyl or C1-10 alkoxycarbonyl (especially isobutoxycarbonyl); R4, R5 and R6 are independently selected from hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 haloalkyl, cyano, nitro, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl or SF5; R7 is cyano, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C3-7 halocycloalkyl, C3-7 cyanocycloalkyl, C1-3 alkyl(C3-7)cycoalkyl, C1-3 alkyl(C3-7)halocycloalkyl, C5-6 cycloalkenyl, C3-7 cycloalkyl(C1-6)alkyl, C5-6 cycloalkenyl(C1-6)alkyl, C2-6 haloalkenyl, C1-6 cyanoalkenyl, C1-6 alkoxy(C1-6)alkyl, C3-6 alkenyloxy(C1-6)alkyl, C3-6 alkynyloxy(C1-6)alkyl, aryloxy(C1-6)alkyl, formyl, C1-6 carboxyalkyl, C1-6 alkylcarbonyl(C1-6)alkyl, C2-6 alkenylcarbonyl(C1-6)alkyl, C2-6 alkynylcarbonyl(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, C3-6 alkenyloxycarbonyl(C1-6)alkyl, C3-6 alkynyloxycarbonyl(C1-6)alkyl, aryloxycarbonyl(C1-6)alkyl, C1-6 alkylthio(C1-6)alkyl, C1-6 alkylsulfinyl(C1-6)alkyl, C1-6 alkylsulfonyl(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, aminocarbonyl(C2-6)alkenyl, aminocarbonyl(C2-6)alkynyl, C1-6 alkylaminocarbonyl(C1-6)alkyl, di(C1-6)alkylaminocarbonyl(C1-6)alkyl, C1-6alkylaminocarbonyl(C1-6)alkenyl, di(C1-6)alkylaminocarbonyl(C1-6)alkenyl, alkylaminocarbonyl(C1-6)alkynyl, di(C1-6)alkylaminocarbonyl(C1-6)alkynyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di(C1-6)alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), phenyl(C1-4)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalcyl, C1-6 alkoxy or C1-6 haloalkoxy), phenyl(C2-4)alkenyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-4)alkyl (where the heteroaryl may be substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl(C1-4)alkyl (where the heterocyclyl may be substituted by halo, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), R15O, C1-8 alkylthio, R16R17N or R18ONxe2x95x90C(R19); R2 is hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C1-6 alkynyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 alkoxy (C1-6)alkyl, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsufinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 haloalkyl, cyano, nitro, formyl, CHxe2x95x90NOR11, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl or SF5; or together R1 and R2 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two hetero atoms selected from O, N or S and which may be optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen; R9 is cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl, C3-7 cycloalkyl(C1-6)alkyl, CH2-(C2-6) alkenyl, CH2(C2-6)alknyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 alkylamino, di(C1-6)alkylamino, C1-6 alkylcarbonylamino, C1-6 alkoxycarbonylamino, C1-6 alkoxy, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylthio, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl or OCO(C1-6)alkyl; R10 is hydrogen, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C2-6 haloalkenyl, C3-7 cycloalkyl(C1-6)alkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, C1-6 alkylaminocarbonyl, di(C1-6)alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R20 is C1-6 alkyl, OR23 or NR24R25; R21 is hydrogen, C1-6 alkyl or C1-6 haloalkyl; R22 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, cyano, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl or NR26R27; R8 is hydrogen, halogen, nitro, cyano, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C2-6 haloalkenyl C3-7 cycloalkyl(C1-6)alkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, C1-6 alkylamninocarbonyl, di(C1-6)alkylaminocarbonyl, C1-6 alkoxycarbonyl(C1-6)alkyl, C1-6 alkylcarbonyl(C1-6)alkyl, C1-6 alkylaminocarbonyl(C1-6)alkyl, di(C1-6)alkylaminocarbonyl(C1-6)alkyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), phenyl(C1-6)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or heteroaryl(C1-6)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R23 is C1-6 alkyl or optionally substituted phenyl(C1-2)alkyl; R24 and R25 are, independently, hydrogen, C1-8 alkyl or phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R15 is hydrogen, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy(C1-6)alkyl, phenyl(C1-4)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-4)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl(C1-4)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkoxycarbonyl(C1-6)alkyl or Nxe2x95x90C(CH3)2; R19 is C1-6 alkyl, C1-6 haloalkyl or phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R16 and R17 are, independently, hydrogen, C1-8 alkyl C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkynyl, C3-7 cycloalkyl(C1-4)alkyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl, or R16 and R17 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups; R18 and R11 are, independently, C1-6 alkyl or phenyl(C1-2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); and R26 and R27 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkynyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, carboxy(C1-6)alkyl or phenyl(C1-2)alkyl; or R26 and R27 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups.
It is preferred that A is C1-6 alkylene, C1-6 alkenylene, C1-6 alkylenoxy, oxy(C1-6)alkylene or C1-6 alkylenamino, each of which is optionally substituted by C1-3 alkyl, C1-3 haloalkyl, C1-3 cyanoalkyl, halogen, C1-3 alkoxy, C1-6 alkoxycarbonyl, cyano, xe2x95x90O, xe2x95x90NR20 or xe2x95x90CR21R22; where R20 is C1-6 alkyl, OR23 or NR24R25; R23 is C1-6 alkyl or phenyl(C1-2)alkyl (where the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R24 and R25 are, independently, hydrogen, C1-8 alkyl or phenyl (which may be optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R21 is hydrogen, C1-6 alkyl or C1-6 haloalkyl; R22 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, cyano, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl or NR26R27; and R26 and R27 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkynyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, carboxy(C1-6)alkyl or phenyl(C1-2)alkyl; or R26 and R27 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups; provided that A is not CH2 or CH2O.
A is more preferably C1-4 alkylene (optionally substituted by halogen, C1-3 alkyl or C1-3 alkoxy, xe2x80x94C(O)xe2x80x94 or C1-4 alkyleneoxy (which may be optionally substituted by C1-3 alkyl); provided that A is not CH2 or CH2O.
It is even more preferred that A is C1-2 alkyl-substituted C1-4 alkylene, fluoro-substituted C1-4 alkylene, methoxy-substituted C1-4 alkylene, xe2x80x94C(O)xe2x80x94 or C2-4 alkyleneoxy; still more preferably A is C1-2 alkyl-substituted C1-4 alkylene, fluoro-substituted C1-4 alkylene or methoxy-substituted C1-4 alkylene.
It is further preferred that A is CH(CH3)CH2, CH2CH(CH3), CH(CH3), CHF, CH(OCH3) or CH(CH3)O; further preferred that A is CH(CH3)CH2, CH2CH(CH3), CH(CH3), CHF or CH(CH3)O; it is especially preferred that A is CHF, CH(OCH3) or CH(CH3); and most preferably A is CHF or CH(CH3).
One group of preferred compounds is that where A is optionally fluoro-substituted C1-4 alkylene, xe2x80x94C(O)xe2x80x94 or C2-4 alkyleneoxy, provided that A is not CH2.
B is preferably N.
Y is preferably O or S.
Y is more preferably O.
Z is preferably O or S.
Z is more preferably O.
It is preferred that R1 is hydrogen, halogen, C1-6 alkyl, C1-6 cyanoalkyl, C1-6 haloalkyl, C3-7 cycloalkyl(C1-4)alkyl, C1-6 alkoxy(C1-6)alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C3-6 cycloalkyl, cyano, nitro or SF5.
R1 is more preferably hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C3-6 cycloalkyl, cyano, nitro or SF5.
It is even more preferred that R1 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C2-6 alkenyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C3-6 cycloalkyl or cyano.
It is most preferred that R1 is halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy.
It is preferred that R2 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C2-6 alkenyl, C1-6 alkynyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, cyano, nitro, formyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl or CHxe2x95x90NOR11 or SF5; or R1 and R2 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated, carbocylic or heterocyclic ring which may contain one or two heteroatoms selected from O, N or S and which is optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen; where R11 is phenyl(C1-2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or C1-6 alkyl.
It is more preferred that R2 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy (C1-6)alkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio or SF5; or R1 and R2 together with the atoms to which they are attached form a cyclopentane or benzene ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen.
R2 is even more preferably hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkoxy(C1-6)alkyl, C1-6 alkylthio or SF5; or R1 and R2 together with the atoms to which they are attached form a benzene ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen; or alternatively the ring may be a cyclopentane ring.
It is further preferred that R2 is hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxy, C1-6 haloalkoxy, or R1 and R2 together with the atoms to which they are attached form a cyclopentane ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen.
R2 is most preferably halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 alkoxy(C1-6)alkyl or C1-6 haloalkoxy.
It is preferred that R3 is hydrogen, C1-10 alkyl, C1-6 alkylcarbonyloxy(C1-6)alkyl, benzoyloxymethyl (where the phenyl ring is optionally substituted with halogen or C1-4 alkyl), C1-6 alkoxy(C1-6)alkyl (where the alkyl group is optionally substituted by aryl or C1-4 alkoxycarbonyl), C2-6 alkenyloxy(C1-4)alkyl, C2-6 alkynyloxy(C1-4)alkyl, benzyloxy(C1-4)alkyl (where the phenyl ring is optionally substituted with halogen or C1-4 alkyl), C3-7 cycloalkyl(C1-4)alkyl, heteroaryl(C1-3)alkyl (where the heteroaryl group is optionally substituted with halogen), tri(C1-4)alkylsilyl(C1-6)alkyl, C2-6 alkenyl(C1-6)alkyl (especially allyl), C2-6 haloalkenyl(C1-6)alkyl, C1-4 alkoxycarbonyl(C2-6)alkenyl(C1-6)alkyl, C2-6 alkynyl(C1-6)alkyl, tri(C1-6)alkylsilyl(C2-6)alkynyl(C1-6)alkyl or C1-10 alkylcarbonyl.
It is further preferred that R3 is hydrogen, C1-6 alkyl, C1-6 alkylcarbonyloxymethyl, benzoyloxymethyl (where the phenyl ring is optionally substituted with halogen or C1-4 alkyl), C1-6 alkoxymethyl, C2-6 alkenyloxymethyl, C2-6 alkynyloxymethyl, benzyloxymethyl (where the phenyl ring is optionally substituted with halogen or C1-4 alkyl), C2-6 alkynyl(C1-6)alkyl (especially propargyl) or C1-10 alkylcarbonyl.
R3 is more preferably hydrogen, C1-6 alkyl, C1-6 alkoxy(C1-6)alkyl, benzyloxymethyl or benzoyloxymethyl; or alternatively R3 may be C1-6 alkylcarbonyloxymediyl.
It is most preferred that R3 is hydrogen, C1-6 alkyl, C1-6 alkylcarbonyloxymethyl or C1-6 alkoxymethyl.
It is preferred that R4, R5 and R6 are, independently, hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, cyano, nitro, C1-6 alkylcarbonyl or C1-6 alkoxycarbonyl.
It is more preferred that R4, R5 and R6 are, independently, hydrogen, halogen or C1-3 alkyl.
It is even more preferred that R4, R5 and R6 are, independently, hydrogen or halogen (especially fluorine).
It is preferred that R7 is cyano, C1-8 alkyl, C1-8 haloalkyl, C1-8 cyanoalkyl, C3-7 cycloalkyl(C1-6)alkyl, C5-6 cycloalkenyl(C1-6)alkyl, C1-6 alkoxy(C1-6)alkyl, C3-6 alkenyloxy(C1-6)alkyl, C3-6 alkynyoxy(C1-6)alkyl, aryloxy(C1-6)alkyl, C1-6 carboxyalkyl, C1-6 alkylcarbonyl(C1-6)alkyl, C2-6 alkenylcarbonyl(C1-6)alkyl, C2-6 alkynylcarbonyl(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, C3-6 alkenyloxycarbonyl(C1-6)alkyl, C3-6 alkynyloxycarbonyl(C1-6)alkyl, aryloxycarbonyl(C1-6)alkyl, C1-6 alkylthio(C1-6)alkyl, C1-6 alkylsulfinyl(C1-6)alkyl, C1-6 alkylsulfonyl(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, C1-6 alkylaminocarbonyl(C1-6)alkyl, di(C1-6)alkylaminocarbonyl(C1-6)alkyl, phenyl(C1-4)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-4)alkyl (where the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6, alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl(C1-4)alkyl (where the heterocyclyl group is optionally substituted by halo, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C2-6 alkenyl, C2-6 haloalkenyl, C1-6 cyanoalkenyl, C5-6 cycloalkenyl, aminocarbonyl(C2-6)alkenyl, C1-6 alkylaminocarbonyl(C1-6)alkenyl, di(C1-6)alkylaminocarbonyl(C1-6)alkenyl, phenyl(C2-4)alkenyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C2-6 alkynyl, aminocarbonyl-(C2-6)alkynyl, alkylaminocarbonyl(C1-6)alkynyl, di(C1-6)alkylaminocarbonyl(C1-6)alkynyl, C3-7 cycloalkyl, C3-7 halocycloalkyl, C3-7 cyanocycloalkyl, C1-3 alkyl(C3-7)cycloalkyl, C1-3 alkyl(C3-7)halocycloalkyl, C5-6 cycloalkenyl, formyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di(C1-6)alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-8 alkylthio, R15O, R16R17N or R18ONxe2x95x90C(R19); where R15 is hydrogen, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C1-6 alkoxy(C1-6)alkyl, phenyl(C1-4)alkyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-4)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl(C1-4)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkoxycarbonyl(C1-6)alkyl, C2-6 alkenyl, C2-6 alkynyl or Nxe2x95x90C(CH3)2; R19 is phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkyl or C1-6 haloalkyl; R16 and R17 are, independently, hydrogen, C1-8 alkyl, C3-7cycloalkyl(C1-4)alkyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkynyl or C1-6 alkoxycarbonyl; and R18 is phenyl(C1-2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or C1-6 alkyl.
R7 is more preferably C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C3-7 halocycloalkyl, C3-7 cyanocycloalkyl C1-3 alkyl(C3-7)cycoalkyl, C1-3 alkyl(C3-7)halocycloalkyl, C5-6 cycloalkenyl, C3-7 cycloalkyl(C1-6)alkyl, C5-6 cycloalkenyl(C1-6)alkyl, C2-6 haloalkenyl, C1-6cyanoalkenyl, C1-6 alkoxy(C1-6)alkyl, C3-6 alkenyloxy(C1-6)alkyl, C3-6 alkynyloxy(C1-6)alkyl, aryloxy(C1-6)alkyl, C1-6 carboxyalkyl, C1-6 alkylcarbonyl(C1-6)alkyl, C2-6 alkenylcarbonyl(C1-6)alkyl, C2-6 alkyncarbonyl(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, C3-6 alkenyloxycarbonyl(C1-6)alkyl, C3-6 alkynyloxycarbonyl(C1-6)alkyl, aryloxycarbonyl(C1-6)alkyl, C1-6 alkylthio(C1-6)alkyl, C1-6 alkylsulfinyl(C1-6)alkyl, C1-6 alkylsulfonyl(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, aminocarbonyl(C2-6)alkenyl, aminocarbonyl(C2-6)alkynyl, C1-6 alkylaminocarbonyl(C1-6)alkyl, di(C1-6)alkylaminocarbonyl(C1-6)alkyl, C1-6 alkylaminocarbonyl(C1-6)alkenyl, di(C1-6)alkylaminocarbonyl(C1-6)alkenyl, alkylaminocarbonyl(C1-6)alkynyl, di(C1-6)alkylaminocarbonyl(C1-6)alkynyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), phenyl(C1-4)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), phenyl(C2-4)alkenyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-4)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl(C1-4)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), R15O, C1-8 alkylthio, R16R17N or R18ONxe2x95x90C(R19); where R15 is C1-8 alkyl, C1-6 haloalkyl; R19 is C1-6 alkyl, C1-6 haloalkyl or phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); R16 and R17 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkynyl, C3-7 cycloalkyl(C1-4)alkyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl, or R16 and R17 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups; and R18 is C1-6 alkyl or phenyl(C1-2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy); and R7 is more preferably C1-8 alkyl, C1-8 haloalkyl, C1-8 cyanoalkyl, C3-7 cycloalkyl, C1-3 alkyl(C3-7)cycloalkyl, C1-6 alkoxy(C1-6)alkyl, heterocyclyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or R16R17N; where R16 and R17 are, independently, C1-8 alkyl or together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups.
It is further preferred that R7 is C1-8 alkyl, C1-8 haloalkyl, C1-8 cyanoalkyl, C3-7 cycloalkyl(C1-6)alkyl, C5-6 cycloalkenyl(C1-6)alkyl, C1-6 alkoxy(C1-6)alkyl, C3-6 alkenyloxy(C1-6)alkyl, C3-6 alkynyloxy(C1-6)alkyl, aryloxy(C1-6)alkyl, C1-6 carboxyalkyl, C1-6 alkylcarbonyl(C1-6)alkyl, C2-6 alkenylcarbonyl(C1-6)alkyl, C2-6 alkynylcarbonyl(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, C3-6 alkenyloxycarbonyl(C1-6)alkyl, C3-6 alkynyloxycarbonyl-(C1-6)alkyl, aryloxycarbonyl(C1-6)alkyl, C1-6 alkylthio(C1-6)alkyl, C1-6 alkylsulfinyl(C1-6)alkyl, C1-6 alkylsulfonyl(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, C1-6 alkylaminocarbonyl(C1-6)alkyl, di(C1-6)alkylaminocarbonyl(C1-6)alkyl, phenyl(C1-6)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-4)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl(C1-4)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C2-6 alkenyl, C2-6 haloalkenyl, C1-6 cyanoalkenyl, C5-6 cycloalkenyl, aminocarbonyl(C2-6)alkenyl, C1-6 alkylaminocarbonyl(C1-6)alkenyl, di(C1-6)alkylaminocarbonyl(C1-6)alkenyl, phenyl(C2-4)alkenyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C2-6 alkynyl, aminocarbonyl(C2-6)alkynyl, alkylaminocarbonyl(C1-6)alkynyl, di(C1-6)alkylaminocarbonyl(C1-6)alkynyl, C3-7 cycloalkyl, C3-7 halocycloalkyl, C3-7 cyanocycloalkyl, C1-3 alkyl(C3-7)cycloalkyl, C1-3 alkyl(C3-7)halocycloalkyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-8 alkylthio, R15O, R16R17N or R18ONxe2x95x90C(R19); where R15 is C1-8 alkyl or C1-6 haloalkyl; R19 is phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkyl or C1-6 haloalkyl; R16 and R17 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl(C1-4)alkyl, C2-6 haloalkyl, C1-6 alkoxy(C1-6)alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkenyl or C1-6 alkoxycarbonyl; and R18 is phenyl(C1-2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or C1-6 alkyl.
It is even more preferred that R7 is C1-8 alkyl, C1-8 haloalkyl, C1-8 cyanoalkyl, C1-6 alkoxy (C1-6) alkyl, C3-7 cycloalkyl, C1-3 alkyl (C3-7) cycloalkyl, heterocyclyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl C1-6 alkoxy or C1-6 haloalkoxy) or di(C1-8)alkylamino.
It is yet more preferred that R7 is C1-8 alkyl, C1-8 haloalkyl, C1-8 cyanoalkyl, C1-6 alkoxy (C1-6) alkyl, C3-7 cycloalkyl, C1-3 alkyl (C3-7) cycloalkyl, heterocyclyl (optionally substituted by C1-6 alkyl) or di(C1-8)alkylamino.
R7 is most preferably C1-8 alkyl, C1-8 haloalkyl, C1-8 cyanoalkyl, C3-7 cycloalkyl, C1-3 alkyl(C3-7)cycloalkyl, C1-6 alkoxy(C1-6)alkyl or R16R17N; where R16 and R17 are, independently, C1-8 alkyl or together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one further heteroatom selected from O, N or S and which may be optionally substituted by one or two C1-6 alkyl groups.
It is preferred that R8 is hydrogen, halogen, nitro, cyano, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C3-7 cycloalkyl(C1-6)alkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl(C1-6)alkyl, C1-6 alkylcarbonyl(C1-6)alkyl, C1-6 alkylaminocarbonyl(C1-6)alkyl, di(C1-6)alkylamino-carbonyl(C1-6)alkyl, phenyl(C1-6)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl(C1-6)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, C1-6 alkylaminocarbonyl, di(C1-6)alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy).
It is more preferred that R8 is hydrogen, halogen, C1-8 alkyl or C1-6 haloalkyl.
It is preferred that R9 is cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl(C1-6)alkyl, C3-7 cycloalkyl, CH2(C2-6)alkenyl, CH2(C2-6)alkynyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 alkylamino, di(C1-6)alkylamino, C1-6 alkylcarbonylamino, C1-6 alkoxycarbonylamino, C1-6 alkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl or (C1-6)alkylcarbonyloxy.
It is preferred that R10 is hydrogen, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C3-7 cycloalkyl(C1-6)alkyl, C1-6 alkoxy(C1-6)alkyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, C1-6 alkylaminocarbonyl, di(C1-6)alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy).
It is more preferred that R10 is hydrogen, C1-8 alkyl or C1-6 haloalkyl.
The compounds in Tables 1-102 illustrate compounds of the invention.
Table 1 provides 160 compounds of formula (1) 
wherein R1, R3 and R7 are defined in Table 1.
Table 95 provides 80 compounds of formula (95) 
wherein R3 and R7 are defined in Table 95.
The following abbreviations are used throughout this description:
Table 103 shows selected melting point and selected NMR data, all with CDCl3 as the solvent (unless otherwise stated; if a mixture of solvents is present, this is indicated as, for example, (CDCl3/d6-DMSO)), (no attempt is made to list all characterising data in all cases) for compounds of Tables 1-102.
The compounds of the invention may be made in a variety of ways.
For example, a compound of formula (I) which is a compound of formula (A) (where A, B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above for a compound of formula (I) except that R3 is not H) may be made from a compound of formula (B) (where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) by treatment with an alkylating agent (such as an alkyl halide, dialkyl sulfate or trialkyloxonium salt), an acylating agent (such as an acid chloride) or a similar reagent (such as a carbamoyl chloride or sulfenyl chloride), optionally in the presence of a base. Frequently these reactions give rise to a mixture of a compound of formula (A) with a compound of formula (C) as an isomeric product. A compound of formula (A) may be separated from a compound of formula (C) and purified by routine techniques (such as recrystallisation, chromatography or trituration with a suitable solvent). 
A compound of formula (A) (where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and where R3 is alkoxyalkyl or acyloxyalkyl) may also be prepared from a compound of formula (B) (where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) by sequential reaction with formaldehyde and an alkylating or acylating agent.
A compound of formula (B) (where B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and A is optionally substituted alkylene, alkenylene, alkynylene, alkylenoxy, alkylenamino or alkylenethio) may be prepared by reacting a compound of formula (II) (where R1 and R2 are as defined above for a compound of formula (I)) either with an appropriate compound of formula (III) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I); A is optionally substituted alkylene, alkenylene, alkynylene, alkylenoxy, alkylenamino or alkylenethio; and X is OH) preferably in the presence of a suitable coupling reagent (such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide or 1,1xe2x80x2-carbonyldiimidazole) or with a suitable compound of formula (III) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I); A is optionally substituted alkylene, alkenylene, alkynylene, alkylenoxy, alkylenamino or alkylenethio; and X is halogen, acyloxy, alkoxy (especially methoxy), substituted alkoxy or aryloxy) optionally in the presence of a base (such as triethylamine or sodium methoxide) and in a suitable solvent (such as 1,1,2,2-tetrachloroethane, tetrahydrofuran, N,N-dimethylacetamide or mesitylene). A compound of formula (B) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I); and A is optionally substituted oxyalkylene) may be prepared in an analogous manner starting from a compound of formula (II) (where R1 and R2 are as defined above for a compound of formula (I)) and a suitable compound of formula (III) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I); A is optionally substituted oxyalkylene; and X is chloro). 
Compounds of formula (II) (where R1 and R2 are as defined above for a compound of formula (I)) are known compounds or may be made from known compounds by known methods.
A compound of formula (III) (where A, B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and X is C1-6 alkoxy [optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)]) may be prepared in a number of ways; the preferred method is dependent on the nature of its fused benzheterocyclic ring and on the nature of its moiety Axe2x80x94C(O)xe2x80x94X (where A and X are as defined above). For example, a suitable reagent Yxe2x80x94C(O)xe2x80x94X (where X is C1-6 alkoxy [optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)]) and Y is a suitably reactive moiety, such as one of those described below) can be attached to a preformed fused heterocyclic ring. Examples of such procedures include, but are not restricted to, the following:
(i) Coupling a compound of formula (IV) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and T is hydroxy) with a compound of formula (V) [where X is C1-6 alkoxy (optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)), Y1 is optionally substituted C1-6 alkylene and Hal is chloro, bromo or iodo] under basic conditions to give a compound of formula (IIIxe2x80x2): 
(ii) Coupling a suitably functionalised alkane (such as a malonate), alkene (such as an acrylate) or alkyne with a suitable fused heterocyclic halide (especially bromide or iodide) under transition-metal (especially Cu or Pd) mediated cross-coupling conditions. An example of this type of transformation is the reaction between a compound of formula (VI) [where Rx and Ry are as defined above for substituents on alkenylene, Y2 is a single bond or is optionally substituted C1-4 alkylene and X is C1-6 alkoxy (optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro))] and a compound of formula (IV) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and T is chlorine, bromine or iodine) under Pd(0) catalysis to give a compound of formula (IIIxe2x80x3): 
and
(iii) Direct alkylation or acylation under, for example, Friedel-Craft conditions.
Certain compounds of formula (III) are amenable to modification to give further analogues. For example, a compound of formula (III) (where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I), X is C1-6 alkoxy [optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)] and A is C1-6 alkylene) undergoes reactions typical of aliphatic esters. Thus a compound of formula (IIIa) [where J is a single bond or a suitable alkylene moiety (such as CH2)] may be reacted with a suitable base (such as lithium diisopropylamide, sodium hydride or lithium hexamethyldisilazide) in a suitable solvent (such as tetrahydrofuran) and then treated with an electrophilic reagent such as an alkylating agent (for example an alkyl halide, alkenylalkyl halide or arylalkyl halide), a halogenating agent (for example N-fluorobenzenesulfonimide) or a further compound with the general formula Rfxe2x80x94LG (where LG designates a suitable leaving group, such as a halide and Rf is, for example, a sulfenyl or acyl moiety) to introduce Rf as a new substituent This procedure may be repeated to introduce a second substituent, Rg (which may be the same or different to Rf): 
As expected, a compound of formula (III), bearing fragments which are sufficiently chemically reactive, undergoes reactions typical of those fragments. For example, a compound of formula (IIId) [where B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I), X is C1-6 alkoxy (optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)) and J is a single bond or a suitable alkylene moiety (such as CH2)] will undergo certain reactions typical of xcex1-ketoesters; for instance, reduction by a metal hydride (such as sodium borohydride) in a suitable solvent (such as ethanol) to give a corresponding alcohol: 
In an alternative preparation of a compound of formula (III) (where A, B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and X is hydroxy or C1-6 alkoxy [optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)]) the benzofused heterocyclic ring may be formed by ring synthesis from a suitably substituted benzene of formula (VII) (where Q and G are suitable precursors (atoms or groups) for the formation of the desired heterocyclic ring, A, R4, R5 and R6 are as defined above for a compound of formula (I) and X is hydroxy or C1-6 alkoxy [optionally substituted by halogen, C1-3 alkoxy, C1-3 alkylthio, tri(C1-3)alkylsilyl or aryl (itself optionally substituted by C1-3 alkyl, C1-3 alkoxy, halogen, cyano or nitro)]): 
This methodology may be extended to the following transformation: 
where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and Q and G are suitable precursors (atoms or groups) for the formation of the desired heterocyclic ring. For example, when Q is hydroxy and G is amino, treatment of a compound of formula (VIII) either with an acylating agent [such as an acid chloride or anhydride] optionally in the presence of a suitable base (such as triethylamine, potassium carbonate or pyridine) or with an acid (preferably in the presence of a coupling agent (such as 1,3-dicyclohexyl-carbodiimide, 1,3-diisopropylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide or 1,1xe2x80x2-carbonyldiimidazole)) followed by cyclisation, optionally catalysed by an acid (such as para-toluenesulfonic acid), gives a benzoxazole: 
Similar reactions (where G is amino and Q is SH or amino) lead to a benzothiazole or a benzimidazole respectively. Indeed, the synthesis of a substituted benzimidazole, benzoxazole or benzothiazole from a substituted benzene is well known [see for example, Alan R. Katritzky and Charles W. Rees (Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, 1984); Helmut M. Hugel, Synth. Commun. (15 (12), 1075-1080, (1985)); J. Scheigetz, R. Zboni and B. Roy, Synth. Commun., 25 (18), 2791-2806, (1995); David W. Dunwell, Delme Evans, Terence A. Hicks (J. Med. Chem., 1975, 18, No. 1, 53); Abdou O. Abdelhamid, Cyril Parkanyi, S. M. Khaledur Rashid and Winston D. Lloyd (J. Heterocyclic Chem., 25, 403, (1988)); Teruyuki Kondo, Sungbong Yang, Keun-Tae Huh, Masanobu Kobayashi, Shinju Kotachi and Yoshihisa Watanabe (Chemistry Letters, 1275, 1991); and Dale L. Boger (J. Org. Chem., 43, No 11, 2296, 1978)] and similar processes may be utilised in the synthesis of a compound of formula (III) (where A, B, Z, R4, R5, R6 and R7 are as defined above for a compound of formula (1) and X is hydroxy, halogen, acyloxy, alkoxy, substituted alkoxy or aryloxy) from appropriate starting materials. A benzothiopbene may be made from an appropriate thiophenol by a process similar to those described by Robert D Schuetz and Richard L Titus (J. Heterocycl. Chem., 4, No 4, 465 (1967); suitable thiophenols are known compounds or may be prepared by known methods from known compounds. A benzofuran may be made from an orthohalophenol, as described by Henning Lutjens and Peter J Scammells (Tetrahedron Letters 39 (1998), 6581-6584); Terence C Owen et al., (Tetrahedron Letters 30, No 13, 1597 (1989)); and Fred G Scbreiber and Robert Stevenson (J. C. S. Perkin 1, 90, 1977). An indole may be made from an ortho-haloaniline according to the methods of Cheng-yi Chen et al. (J. Org. Chem 1997, 62, 2676); Takao Sakamoto et al., (J. Org. Chem. 1997, 62, 6507); and Alan D. Adams et al. (WO9827974).
A compound of formula (I) (where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above, Y is S and R3 is H) may be prepared by reacting a compound of formula (I) (where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above, Y is O and R3 is H) with a suitable thionating agent (such as 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson""s reagent), 2,4-bis(methylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Davy reagent methyl), 2,4-bis(para-tolyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Davy reagent p-tolyl) or phosphorus pentasulfide) in a suitable solvent (such as toluene or fluorobenzene).
A compound of formula (IX) (where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) may be made by reacting a compound of formula (X) (where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above) with N,N-dimethyl-formamide dialkyl acetal in a suitable solvent (such as toluene or N,N-dimethylformamide). Frequently this reaction produces a mixture of E- and Z-isomers which are sometimes separable by standard techniques (such as flash column chromatography and recrystallisation). 
A compound of formula (X) ((where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined for a compound of formula (I)) may be treated in an analogous manner with a trialkylorthoformate to afford a compound of formula (XI) (where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined for a compound of formula (I) and Rd is C1-6 alkyl). 
A compound of formula (I) (where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) may be treated with an amine of formula (HNR26R27) (where R26 and R27 are as defined for a compound of formula (I)) to give a compound of formula (XII) (where B, Z, R1, R2, R3, R4, R5, R6 and R7, R26 and as defined above for a compound of formula (I)).
A compound of formula (IX) (where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) may be oxidised to a compound of formula (XIII) (where B, Z, R1, R2, R3, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) under known conditions. 
A compound of formula (I) (where Y is S, R3 is H and A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I)) may be treated with an electrophile (such as an alkyl halide, dialkyl sulfate, chloromethyl ether or trialkyloxonium salt) optionally in the presence of a base to give a compound of formula (XIV) (where R32 is alkyl, alkenylalkyl, alkynylalkyl, cycloalkyl, alkoxyalkyl and A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I)). Such a compound may be further treated with a compound of formula R9xe2x80x94NH2 (where R9 is as defined above for a compound of formula (I)) optionally in the presence of a mercuric salt (such as mercuric chloride), according to known procedures to give a compound of formula (XV) (where R3 is H and A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I)). Such a compound may be treated with an alkylating agent, an acylating agent or similar electrophile to give a compound of formula (XV) [where A, B, Z, R1, R2, R4, R5, R6 and R7 are as defined above for a compound of formula (I) and R3 is as defined above for a compound of formula (I) (except that R3 is not H)] in an analogous manner to that previously described for the formation of a compound of formula (A) from a compound of formula (B). 
The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fibre products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
Examples of pest species which may be controlled by the compounds of formula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nitaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidella spp. (scale insects), Trialeurodes spp. (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis (European corn borer), Spodoptera littoralis (cotton leafworm), Heliothis virescens (tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pieris brassicae (white butterfly), Plutella xylostella (diamond back moth), Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locusta migratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp. (rootworms), Panonychus ulmi (European red mite), Panonychus citri (citrus red mite), Tetranychus urticae (two-spotted spider mite), Tetranychus cinnabamus (carmine spider mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalides felis (cat flea), Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes), Lucillia spp. (blowflies), Blattelia germanica (cockroach), Periplaneto americana (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae (for example Mastotermes spp.), the Kalotermitidae (for example Neotermes spp.), the Rhinotermitidae (for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulphureus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh""s ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root knot nematodes), Globodera spp. and Heterodera spp. (cyst nematodes), Pratylenchus spp. (lesion nematodes), Rhodpholus spp. (banana burrowing nematodes), Tylenchulus spp.(citrus nematodes), Haemonchus contortus (barber pole worm), Caenorhabditis elegans (vinegar eelworm), Trichostrongylus spp. (gastro intestinal nematodes) and Deroceras reticulatum (slug).
The compounds of formula (I) are also active fungicides and may be used to control one or more of the following pathogens: Pyricularia oryzae (Magnaporthe grisea) on rice and wheat and other Pyricularia spp. on other hosts; Puccinia recondita, Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts (for example turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants); Erysiphe cichoracearum on cucurbits (for example melon); Erysiphe graminis (powdery mildew) on barley, wheat, rye and turf and other powdery mildews on various hosts, such as Sphaerotheca macularis on hops, Sphaerotheca fusca (Sphaerotheca fuliginea) on cucurbits (for example cucumber), Leveillula taurica on tomatoes, aubergine and green pepper, Podosphaera leucotricha on apples and Uncinula necator on vines; Cochliobolus spp., Helminthosporium spp., Drechslera spp. (Pyrenophora spp.), Rhynchosporium spp., Mycosphaerella graminicola (Septoria tritici) and Phaeosphaeria nodorum (Stagonospora nodorum or Septoria nodorum), Pseudocercosporella herpotrichoides and Gaeumannomyces graminis on cereals (for example wheat, barley, rye), turf and other hosts; Cercospora arachidicola and Cercosporidium personatum on peanuts and other Cercospora spp. on other hosts, for example sugar beet, bananas, soya beans and rice; Botrytis cinerea (grey mould) on tomatoes, strawberries, vegetables, vines and other hosts and other Botrytis spp. on other hosts; Alternaria spp. on vegetables (for example carrots), oil-seed rape, apples, tomatoes, potatoes, cereals (for example wheat) and other hosts; Venturia spp. (including Venturia inaequalis (scab)) on apples, pears, stone fruit, tree nuts and other hosts; Cladosporium spp. on a range of hosts including cereals (for example wheat) and tomatoes; Monilinia spp. on stone fruit, tree nuts and other hosts; Didymella spp. on tomatoes, turf, wheat, cucurbits and other hosts; Phoma spp. on oil-seed rape, turf, rice, potatoes, wheat and other hosts; Aspergillus spp. and Aureobasidium spp. on wheat, lumber and other hosts; Ascochyta spp. on peas, wheat, barley and other hosts; Stemphylium spp. (Pleospora spp.) on apples, pears, onions and other hosts; summer diseases (for example bitter rot (Glomerella cingulata), black rot or frogeye leaf spot (Botryosphaeria obtusa), Brooks fruit spot (Mycosphaerella pomi), Cedar apple rust (Gymnosporangium juniperi-virginianae), sooty blotch (Gloeodes pomigena), flyspeck (Schizothyrium pomi) and white rot (Botryosphaeria dothidea)) on apples and pears; Plasmopara viticola on vines; other downy mildews, such as Bremia lactucae on lettuce, Peronospora spp. on soybeans, tobacco, onions and other hosts, Pseudoperonospora humuli on hops and Pseudoperonospora cubensis on cucurbits; Pythium spp. (including Pythium ultimum) on turf and other hosts; Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts; Thanatephorus cucumeris on rice and turf and other Rhizoctonia spp. on various hosts such as wheat and barley, peanuts, vegetables, cotton and turf; Sclerotinia spp. on turf, peanuts, potatoes, oil-seed rape and other hosts; Sclerotium spp. on turf, peanuts and other hosts; Gibberella fujikuroi on rice; Colletotrichum spp. on a range of hosts including turf, coffee and vegetables; Laetisaria fuciformis on turf; Mycosphaerella spp. on bananas, peanuts, citrus, pecans, papaya and other hosts; Diaporthe spp. on citrus, soybean, melon, pears, lupin and other hosts; Elsinoe spp. on citrus, vines, olives, pecans, roses and other hosts; Verticillium spp. on a range of hosts including hops, potatoes and tomatoes; Pyrenopeziza spp. on oil-seed rape and other hosts; Oncobasidium theobromae on cocoa causing vascular streak dieback; Fusarium spp., Typhula spp., Microdochium nivale, Ustilago spp., Urocystis spp., Tilletia spp. and Claviceps purpurea on a variety of hosts but particularly wheat, barley, turf and maize; Ramularia spp. on sugar beet, barley and other hosts; post-harvest diseases particularly of fruit (for example Penicillium digitatum, Penicillium italicum and Trichoderma viride on oranges, Colletotrichum musae and Gloeosporium musarum on bananas and Botrytis cinerea on grapes); other pathogens on vines, notably Eutypa lata, Guignardia bidwellii, Phellinus igniarus, Phomopsis viticola, Pseudopeziza tracheiphila and Stereum hirsutum; other pathogens on trees (for example Lophodermium seditiosum) or lumber, notably Cephaloascus fragrans, Ceratocystis spp., Ophiostoma piceae, Penicillium spp., Trichoderma pseudokoningii, Trichoderma viride, Trichoderma harzianum, Aspergillus niger, Leptographium lindbergi and Aureobasidium pullulans; and fungal vectors of viral diseases (for example Polymyxa graminis on cereals as the vector of barley yellow mosaic virus (BYMV) and Polymyxa betae on sugar beet as the vector of rhizomania).
A compound of formula (I) may move acropetally, basipetally or locally in plant tissue to be active against one or more fungi. Moreover, a compound of formula (I) may be volatile enough to be active in the vapour phase against one or more fungi on the plant.
The invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, or to a plant susceptible to attack by a pest, and a method of combating and controlling fungi which comprises applying a fungicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a plant, to a seed of a plant, to the locus of the plant or seed, to soil or to any other growth medium (for example a nutrient solution). The compounds of formula (I) are preferably used against insects, acarines, nematodes or fungi.
The term xe2x80x9cplantxe2x80x9d as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes protectant, curative, systemic, eradicant and antisporulant treatments.
As fungicides, the compounds of formula (I) are preferably used for agricultural, horticultural and turfgrass purposes in the form of a composition.
In order to apply a compound of formula (I) as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, or, as a fungicide to a plant, to a seed of a plant, to the locus of the plant or seed, to soil or to any other growth medium, a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (I). The composition is generally used for the control of pests or fungi such that a compound of formula (I) is applied at a rate of from 0.1 g 10 kg per hectare, preferably from 1 g to 6 kg per hectare, more preferably from 1 g to 1 kg per hectare.
When used in a seed dressing, a compound of formula (I) is used at a rate of 0.0001 g to 10 g (for example 0.001 g or 0.05 g), preferably 0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogram of seed.
In another aspect the present invention provides an insecticidal, acaricidal, nematicidal, molluscicidal or fungicidal composition comprising an insecticidally, acaricidally, nematicidally, molluscicidally or fungicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, acaricidal, nematicidal or fungicidal composition.
In a still further aspect the invention provides a method of combating and controlling pests or fungi at a locus which comprises treating the pests or fungi or the locus of the pests or fungi with an insecticidally, acaricidally, nematicidally, molluscicidally or fungicidally effective amount of a composition comprising a compound of formula (I). The compounds of formula (I) are preferably used against insects, acarines, nematodes or fungi.
The compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
Dustable powders (DP) may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
Soluble powders (SP) may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
Wettable powders (WP) may be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).
Granules (GR) may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller""s earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
Dispersible Concentrates (DC) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank).
Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol),
N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as C8-C10 fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70xc2x0 C.) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of formula (I) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane). A compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.
A compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment. A compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
A composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
A compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or olefine sulphonates, taurates and lignosulphonates.
Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
A compound of formula (I) may be applied by any of the known means of applying pesticidal or fungicidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment
A compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
A compound of formula (I) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers). Suitable formulation types include granules of fertiliser. The mixtures suitably contain up to 25% by weight of the compound of formula (I).
The invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula (I).
The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
By including another fungicide, the resulting composition may have a broader spectrum of activity or a greater level of intrinsic activity than the compound of formula (I) alone. Further the other fungicide may have a synergistic effect on the fungicidal activity of the compound of formula (I).
The compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition. Examples of suitable pesticides include the following:
a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate;
b) Organophosphates, such as, profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon;
c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl or oxamyl;
d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron;
e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or azocyclotin;
f) Pyrazoles, such as tebufenpyrad and fenpyroximate;
g) Macrolides, such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad or azadirachtin;
h) Hormones or pheromones;
i) Organochlorine compounds such as endosulfan, benzene hexachloride, DDT, chlordane or dieldrin;
j) Amidines, such as chlordimeform or amitraz;
k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam;
l) Chloronicotinyl compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram or thiamethoxam;
m) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide;
n) Diphenyl ethers, such as diofenolan or pyriproxifen;
o) Indoxacarb;
p) Chlorfenapyr, or
q) Pymetrozine.
In addition to the major chemical classes of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
Examples of fungicidal compounds which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide, xcex1-[N-(3-chloro-2,6-xylyl)-2-methoxyacetiamido]-xcex3-butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916, cyamidazosulfamid), 3-5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281, zoxamide), N-alkyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide (MON65500), N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionanide (AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate, copper tallate and Bordeaux mixture, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulphide 1,1xe2x80x2-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl(Z)-N-benzyl-N([methyl(methyl-thioethylideneaminooxycarbonyl)amino]thio)-xcex2-alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulphur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifuzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram, timibenconazole, toiclofos-methyl, tolyifluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb and ziram.
The compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imnidazole.
Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIX(trademark).
Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.